5-Chloro-1-indanylamine (also named as 5-chloro-1-aminoindane) is disclosed in Chem. Abstr., 60, 1716g (1964). This compound, as well as others disclosed in that publication, are stated to be anti-allergic, anti-spasmodic and local anesthetic drugs.
U.S. Pat. No. 3,988,339 discloses tetrahydroisoquinoline compounds useful as phenylethanolamine N-methyl transferase inhibitors (PNMT inhibitors), which isoquinolines may contain 1 or 2 chlorines in addition to various other permitted groupings in the phenyl ring of the tetrahydroisoquinoline ring system.
U.S. Pat. No. 3,919,316 discloses a series of 2-amino-dichlorotetralines, stated to be inhibitors of various enzyme ststems including specifically PNMT.
U.S. Pat. No. 3,637,740 discloses a group of tetrahydro-1-naphthylamines and substituted-1-aminoindanes useful as psycotherapeutic agents. Whereas chlorine is a permissible substituent in the phenyl ring of these tetrahydro-1-naphthylamine or 1-aminoindane derivatives, there is no disclosure therein of compounds which have only a chlorine substituent. For instance, Example I, discloses a 5-methoxy-8-chloro derivative. In addition, although a primary amine group is permissible in the 1-position of the tetrahydro naphthalene or indane ring system, the compounds actually disclosed are, in general, secondary and tertiary amines. Disclosure relevant to the preparation of 1-aminoindanes begins with the Example XXVII. Here again, the phenyl ring of the indane ring system is substituted with both a methoxy and a chlorine, and the final product is an N,N-dimethyl derivative. The Table at the top of column 14 discloses only 2 primary amines, both of the 1-aminoindane series, and these have respectively an OH in the 4-position and an acetyl in the 7-position of the phenyl ring.
There are many references to 1-aminoindane in the non-patent literature. 1-Aminoindane appears in Beilstein, Hanbuch der Organ. Chem, Bd XII, Syst. No. 1709 pg. 1191. Of particular interest is the reference appearing in Chem. Abstr. 62, 1616d (1965) which refers to 1-aminoindane derivatives valuable as anti-depressant and psychostimulating agents. The compounds in question are, in general, N-substituted 1-aminoindanes. Horn and Schenider, publishing in J. Pharm. Exp. Ther, 180, 523-30 (1972), state that 2-aminoindane is a better inhibitor of catechol amine uptake than 1-aminoindane.
2-Aminoindane can be looked upon as a rigid confromational analog of amphetamine and 1-aminoindane can be looked upon as a rigid conformational analog of benzylamine.
Nothing in the above-cited literature would suggest that selected chlorinated 1-aminoindanes would have unexpectedly high activity as inhibitors of N-methyl transferase.